Organic Letters
Letter
Notes
(8) (a) Ratani, T. S.; Bachman, S.; Fu, G. C.; Peters, J. C. J. Am.
Chem. Soc. 2015, 137, 13902. (b) Liang, Y.; Fu, G. C. J. Am. Chem. Soc.
The authors declare no competing financial interest.
2
015, 137, 9523. (c) Kainz, Q. M.; Matier, C. M.; Bartoszewicz, A.;
Zultanski, S. L.; Peters, J. C.; Fu, G. C. Science 2016, 351, 681.
(d) Ahn, J. M.; Ratani, T. S.; Hannoun, K. I.; Fu, G. C.; Peters, J. C. J.
Am. Chem. Soc. 2017, 139, 12716. (e) Zhao, W.; Wurz, R. P.; Peters, J.
C.; Fu, G. C. J. Am. Chem. Soc. 2017, 139, 12153.
ACKNOWLEDGMENTS
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Financial support from the National Natural Science
Foundation of China (21602158, 21372177, and 21472140),
State Key Laboratory of Structural Chemistry (No. 20170037),
Zhejiang Provincial Natural Science Foundation
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9) (a) Rovira, M.; Soler, M.; Guell, I.; Wang, M.-Z.; Gomez, L.;
Ribas, X. J. Org. Chem. 2016, 81, 7315. (b) Sreedhar, B.; Arundhathi,
R.; Reddy, P. L.; Kantam, M. L. J. Org. Chem. 2009, 74, 7951. (c) Zhai,
Y.; Chen, X.; Zhou, W.; Fan, M.; Lai, Y.; Ma, D. J. Org. Chem. 2017,
(
LY16B020011), and Wenzhou Medical University start-up
funding (QTJ15026) and grants from the Opening Project of
Zhejiang Provincial Top Key Discipline of Pharmaceutical
Sciences (201723) and the Xinmiao Talent Planning
Foundation of Zhejiang Province (2017R426045) are greatly
appreciated.
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2, 4964.
10) (a) Shen, Y.; Chen, J.; Liu, M.; Ding, J.; Gao, W.; Huang, X.;
Wu, H. Chem. Commun. 2014, 50, 4292. (b) Min, L.; Wu, G.; Liu, M.;
Gao, W.; Ding, J.; Chen, J.; Huang, X.; Wu, H. J. Org. Chem. 2016, 81,
7584. (c) Luo, D.; Wu, G.; Yang, H.; Liu, M.; Gao, W.; Huang, X.;
Chen, J.; Wu, H. J. Org. Chem. 2016, 81, 4485.
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11) (a) Douglas, J. J.; Albright, H.; Sevrin, M. J.; Cole, K. P.;
Stephenson, C. R. J. Angew. Chem., Int. Ed. 2015, 54, 14898.
b) Nguyen, J. D.; D’Amato, E. M.; Narayanam, J. M. R.; Stephenson,
REFERENCES
■
(
1) (a) Rappoport, Z. The Chemistry of Phenols; Wiley-VCH:
(
Weinheim, Germany, 2003. (b) Tyman, J. H. P. Synthetic and Natural
Phenols; Elsevier: New York, 1996. (c) Hartwig, J. F. In Handbook of
Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.;
Wiley-Interscience: New York, 2002. (d) Kotschy, A.; Timari, G.
́
Heterocycles from Transition Metal Catalysis; Springer: Dordrecht, The
Netherlands, 2005. (e) Enthaler, S.; Company, A. Chem. Soc. Rev.
C. R. J. Nat. Chem. 2012, 4, 854. (c) Narayanam, J. M. R.; Tucker, J.;
Stephenson, C. R. J. Am. Chem. Soc. 2009, 131, 8756.
12) (a) Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski,
(
M. C. Chem. Rev. 2013, 113, 6234. (b) Shi, Z.; Zhang, C.; Tang, C.;
Jiao, N. Chem. Soc. Rev. 2012, 41, 3381. (c) Rolff, M.; Tuczek, F.
Angew. Chem., Int. Ed. 2008, 47, 2344. (d) Cramer, C. J.; Tolman, W.
B. Acc. Chem. Res. 2007, 40, 601. (e) Punniyamurthy, T.; Velusamy, S.;
Iqbal, J. Chem. Rev. 2005, 105, 2329. (f) Gamez, P.; Aubel, P. G.;
Driessen, W. L.; Reedijk, J. Chem. Soc. Rev. 2001, 30, 376.
2
(
(
011, 40, 4912.
2) For Pd-catalyzed hydroxylation of (hetero)aryl halides, see:
a) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.;
Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595.
b) Schulz, T.; Torborg, C.; Schaffner, B.; Huang, J.; Zapf, A.;
Kadyrov, R.; Borner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48,
18. (c) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L.
(
̈
̈
9
Angew. Chem., Int. Ed. 2007, 46, 7251. (d) Anderson, K. W.; Ikawa, T.;
Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
(
e) Cheung, C. W.; Buchwald, S. L. J. Org. Chem. 2014, 79, 5351.
(
f) Yu, C.-W.; Chen, G. S.; Huang, C.-W.; Chern, J.-W. Org. Lett.
2
012, 14, 3688. (g) Lavery, C. B.; Rotta-Loria, N. L.; McDonald, R.;
Stradiotto, M. Adv. Synth. Catal. 2013, 355, 981.
3) For selected references on Cu-catalyzed hydroxylation of
hetero)aryl halides, see: (a) Tlili, A.; Xia, N.; Monnier, F.; Taillefer,
(
(
M. Angew. Chem., Int. Ed. 2009, 48, 8725. (b) Jing, L.; Wei, J.; Zhou,
L.; Huang, Z.; Li, Z.; Zhou, X. Chem. Commun. 2010, 46, 4767.
(
c) Zhao, D.; Wu, N.; Zhang, S.; Xi, P.; Su, X.; Lan, J.; You, J. Angew.
Chem., Int. Ed. 2009, 48, 8729. (d) Thakur, K.; Sekar, G. Chem.
Commun. 2011, 47, 6692. (e) Yang, K.; Li, Z.; Wang, Z.; Yao, Z.; Jiang,
S. Org. Lett. 2011, 13, 4340. (f) Yang, D.; Fu, H. Chem. - Eur. J. 2010,
1
2
6, 2366. (g) Maurer, S.; Liu, W.; Zhang, X.; Jiang, Y.; Ma, D. Synlett
010, 2010, 976. (h) Xia, S.; Gan, L.; Wang, K.; Li, Z.; Ma, D. J. Am.
Chem. Soc. 2016, 138, 13493. (i) Xiao, Y.; Xu, Y.; Cheon, H.-S.; Chae,
J. J. Org. Chem. 2013, 78, 5804. (j) Ding, G.; Han, H.; Jiang, T.; Wu,
T.; Han, B. Chem. Commun. 2014, 50, 9072. (k) Wang, Y.; Zhou, C.;
Wang, R. Green Chem. 2015, 17, 3910.
(
4) (a) Fier, P. S.; Maloney, K. M. Org. Lett. 2016, 18, 2244. (b) Fier,
P. S.; Maloney, K. M. Org. Lett. 2017, 19, 3033. (c) Fier, P. S.;
Maloney, K. M. Angew. Chem., Int. Ed. 2017, 56, 4478.
(
5) (a) Sun, S.; Shang, M.; Wang, H.; Lin, H.; Dai, H.; Yu, J. J. Org.
Chem. 2015, 80, 8843. (b) Zhang, Y.; Yu, J. J. Am. Chem. Soc. 2009,
31, 14654. (c) Yan, Y.; Feng, P.; Zheng, Q.; Liang, Y.; Lu, J.; Cui, Y.;
Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827.
6) Liu, Q.; Wu, P.; Yang, Y.; Zeng, Z.; Liu, J.; Yi, H.; Lei, A. Angew.
Chem. 2012, 51, 4744.
7) For selected reviews on visible-light photoredox catalysis, see:
a) Staveness, D.; Bosque, I.; Stephenson, C. R. J. Acc. Chem. Res.
016, 49, 2295. (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C.
1
(
(
(
2
Chem. Rev. 2013, 113, 5322. (c) Tellis, J. C.; Kelly, C. B.; Primer, D.
N.; Jouffroy, M.; Patel, N. R.; Molander, G. A. Acc. Chem. Res. 2016,
4
9, 1429. (d) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Acc. Chem.
Res. 2016, 49, 1911. (e) Hopkinson, M. N.; Tlahuext-Aca, A.; Glorius,
F. Acc. Chem. Res. 2016, 49, 2261.
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